Senior Enterprise Customer Success Manager

ABOUT PLEO

• Messy spend management is tricky business.
• And tedious processes are a lose-lose situation for all involved, not just finance.
• At Pleo, we're changing that.
• We build spend solutions that make managing money seamless, empowering, and surprisingly effective for finance teams and employees alike - with a vision to help all businesses 'go beyond'.
• The word 'Pleo' actually means 'more than you'd expect', and living by that mantra has been the secret to our success over the last 10 years.
• Now, we're at a pivotal moment in our journey; every move we make has a direct impact on our 40,000+ customers, our business, and our collective success.
• We need people who take pride in uncovering customer needs, who turn complex problems into simple solutions, challenge the way things are done (respectfully), and always aim high.
• With great ambitions driving us forward, we can't say we've got this whole thing figured out.
• And frankly, that's half the fun!
• What we can say is that we're a driven, progressive, and, importantly, a kind bunch of 850+ people from over 100 nationalities, all committed to delivering the future of business spending, together.

ABOUT THE ROLE

• We're looking for a Senior Enterprise Customer Success Manager to join our Customer Experience team at Pleo.
• In this role, you'll own a portfolio of large, complex, and strategically important enterprise customers, helping them achieve measurable business outcomes, expand adoption, manage change, and build long-term value with Pleo.
• You'll serve as a trusted advisor to senior customer stakeholders while coordinating the broader Pleo relationship across Customer Success, Product, Support, Sales, Finance, and other internal teams.
• This is not a reactive account-management role.
• You'll be expected to understand each customer's business priorities, operating model, success criteria, and risk profile.
• You'll turn that understanding into clear success plans, executive engagement strategies, adoption programs, renewal plans, and growth opportunities.
• The right candidate will bring at least three years of direct experience managing enterprise customers, along with the communication skills, commercial judgment, and operational discipline required to manage high-value relationships in a fast-paced technology environment.

WHO YOU'LL BE WORKING WITH AND REPORTING TO

You'll report to our Manager of Customer Success, Large & High-Growth Customers and work closely with teams across:

• Customer Support
• Customer Onboarding
• Sales and Account Management
• Product and Product Operations
• Revenue Operations
• Finance
• Data and Analytics
• Program Management and Operations

• You'll work with customer stakeholders across finance, procurement, operations, technology, transformation, and executive leadership.
• You'll be responsible for creating alignment across these stakeholders, establishing clear governance, and ensuring Pleo remains connected to the customer's evolving strategic and operational priorities.

WHAT YOU'LL BE DOING

As a Senior Enterprise Customer Success Manager, you will:

• Own a portfolio of enterprise customers with accountability for customer health, value realisation, adoption, retention, renewal readiness, advocacy, and growth.
• Build trusted relationships with senior and executive stakeholders, positioning yourself as a credible advisor who understands their business priorities and operating environment.
• Develop detailed customer success plans that connect the customer's strategic goals to measurable outcomes, adoption milestones, responsibilities, and timelines.
• Lead executive business reviews and strategic customer meetings that demonstrate value, address risks, align stakeholders, and create clear next steps.
• Drive product adoption across complex customer organisations, helping customers expand usage across teams, entities, locations, use cases, and workflows.
• Create and maintain detailed stakeholder maps, identifying decision-makers, champions, influencers, operational contacts, blockers, and executive sponsors.
• Identify churn risk early using product usage, engagement, stakeholder, support, financial, organisational, and external business signals.
• Build and execute churn-prevention plans with clear actions, owners, timelines, customer commitments, and executive escalation paths.
• Maintain detailed and accurate forecasts across renewals, risk, customer health, expected outcomes, growth opportunities, and major account milestones.
• Lead renewal-readiness activities by ensuring customer value is documented, risks are addressed, stakeholders are aligned, and commercial partners have accurate account intelligence.
• Identify and support expansion opportunities by connecting additional Pleo capabilities, products, or use cases to the customer's evolving business needs.
• Coordinate complex customer escalations across Support, Product, Engineering, Finance, and other teams while maintaining clear and confident customer communication.
• Act as the customer's internal advocate, ensuring customer needs, feedback, risks, and opportunities are visible to the right stakeholders at Pleo.
• Navigate customer change effectively, including leadership transitions, reorganisations, acquisitions, market expansion, platform changes, and evolving business priorities.
• Track customer commitments and outcomes with strong operational discipline, ensuring actions are documented, owned, and completed.
• Contribute to the evolution of Pleo's enterprise Customer Success model by sharing best practices, customer insights, playbooks, and recommendations.
• Support peer development and knowledge sharing across the Customer Success team without holding direct people-management responsibility.

TO PUT THINGS INTO CONTEXT

In this role, you can expect to work on priorities such as:

• strengthening relationships with Pleo's largest and most strategic customers
• improving enterprise customer retention and renewal predictability
• increasing adoption across complex customer organisations
• creating stronger executive engagement and governance
• identifying churn risk before it becomes a renewal issue
• improving forecast accuracy and account visibility
• coordinating complex customer needs across multiple internal teams
• helping customers quantify and communicate the value they receive from Pleo
• identifying opportunities for expansion and deeper product adoption
• improving the consistency and quality of enterprise success planning
• helping customers navigate operational and organisational change
• turning customer feedback into actionable Product and CX insight

• You can expect to work across a technology environment that includes CRM, Customer Success platforms, support systems, product analytics, business intelligence tools, workflow tools, and collaboration platforms.
• Examples may include Vitally, Gainsight or similar, Zendesk, Looker, Tableau or Power BI, Jira, Asana, and Slack.

WHAT YOU BRING

You'll thrive in this role if you have:

• At least three years of direct enterprise Customer Success or strategic account-management experience, managing large, complex, and high-value B2B customers.
• Five or more years of overall experience in Customer Success, account management, consulting, implementation, or a related customer-facing role.
• Experience working in SaaS, fintech, enterprise technology, or another complex B2B technology environment.
• A proven record of retaining and growing enterprise customers, including managing renewals, adoption, risk, and value realisation.
• Strong executive relationship-management skills, with the confidence and credibility to engage senior decision-makers and business leaders.
• Experience managing complex stakeholder environments involving multiple teams, business units, regions, entities, or decision-makers.
• Strong churn-prediction and prevention skills, including the ability to interpret customer signals, identify root causes, and build effective recovery plans.
• Detailed forecasting experience across renewals, customer risk, account health, adoption, and expansion opportunities.
• Strong commercial judgment, with an understanding of how customer outcomes connect to retention, revenue, expansion, and long-term account value.
• Excellent verbal and written communication skills, including the ability to lead difficult conversations, present to executives, and simplify complex issues.
• Experience building strategic success plans, account plans, stakeholder maps, and executive business reviews.
• Strong analytical skills, with the ability to interpret customer data, product usage, service trends, and business information.
• Strong cross-functional leadership skills, with the ability to align internal stakeholders without relying on direct authority.
• A structured and proactive approach to account management, with excellent follow-through and attention to detail.
• Comfort working in a fast-paced growth environment where customer expectations, internal priorities, and business needs can evolve quickly.
• The ability to balance strategic relationship management with detailed operational execution.

NICE TO HAVE

• Experience in fintech, payments, spend management, financial operations, or expense-management technology
• Experience working with finance leaders, procurement teams, controllers, CFO organisations, or transformation leaders
• Experience managing multi-country or multinational enterprise customers
• Familiarity with ERP, accounting, procurement, or financial-system integrations
• Experience supporting customers through significant organisational or technology transformation
• Exposure to AI-enabled Customer Success, predictive health models, automated risk detection, or digital engagement
• Experience partnering with Product teams on strategic customer feedback and roadmap discussions
• Experience managing accounts with complex security, compliance, governance, or implementation requirements

• WHY IS THIS ROLE A GOOD FIT FOR YOU?
• This role is a good fit for you if:

• You enjoy building strategic relationships with complex enterprise customers.
• You are comfortable engaging senior leaders and navigating high-stakes customer situations.
• You know how to connect product adoption to measurable customer outcomes.
• You are proactive about identifying and addressing churn risk.
• You combine strong relationship skills with rigorous account-management discipline.
• You are confident leading executive reviews, renewal discussions, and difficult customer conversations.
• You enjoy coordinating internal teams around complex customer needs.
• You want direct responsibility for protecting and growing some of Pleo's most important customer relationships.

THIS ROLE IS NOT A GOOD FIT FOR YOU IF:

• You have not directly managed enterprise or strategic customer relationships.
• You prefer transactional or high-volume customer portfolios.
• You are uncomfortable owning customer risk, retention, and renewal readiness.
• You prefer reacting to customer requests rather than building proactive engagement strategies.
• You are uncomfortable engaging executive stakeholders or leading difficult conversations.
• You do not enjoy detailed forecasting, CRM management, and account planning.
• You prefer working independently without significant cross-functional coordination.
• You are looking for a people-management role rather than a senior individual-contributor position.

HOW YOU'LL DEVELOP IN THIS ROLE

IN YOUR FIRST 1 MONTH AT PLEO, YOU'LL:

• Learn Pleo's product, enterprise customer journey, value proposition, and Customer Success operating model.
• Build a detailed understanding of your customer portfolio, including revenue, renewal dates, usage, stakeholders, open issues, risks, and growth potential.
• Establish relationships with key customer stakeholders and internal account partners.
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